diff --git a/api/server/middleware/buildEndpointOption.js b/api/server/middleware/buildEndpointOption.js
index 7205b76473..3de13ed2e6 100644
--- a/api/server/middleware/buildEndpointOption.js
+++ b/api/server/middleware/buildEndpointOption.js
@@ -42,6 +42,15 @@ async function buildEndpointOption(req, res, next) {
       return handleError(res, { text: 'Model spec mismatch' });
     }
 
+    if (
+      currentModelSpec.preset.endpoint !== EModelEndpoint.gptPlugins &&
+      currentModelSpec.preset.tools
+    ) {
+      return handleError(res, {
+        text: `Only the "${EModelEndpoint.gptPlugins}" endpoint can have tools defined in the preset`,
+      });
+    }
+
     const isValidModelSpec = enforceModelSpec(currentModelSpec, parsedBody);
     if (!isValidModelSpec) {
       return handleError(res, { text: 'Model spec mismatch' });
diff --git a/api/server/middleware/enforceModelSpec.js b/api/server/middleware/enforceModelSpec.js
index c2c10b3860..17270a5cf8 100644
--- a/api/server/middleware/enforceModelSpec.js
+++ b/api/server/middleware/enforceModelSpec.js
@@ -24,21 +24,32 @@ const enforceModelSpec = (modelSpec, parsedBody) => {
 
 /**
  * Checks if there is a match for the given key and value in the parsed body
- * or any of its interchangeable keys.
+ * or any of its interchangeable keys, including deep comparison for objects and arrays.
  * @param {string} key
  * @param {any} value
- * @param {TConversation} parsedBody
+ * @param {object} parsedBody
  * @returns {boolean}
  */
 const checkMatch = (key, value, parsedBody) => {
-  if (parsedBody[key] === value) {
+  const isEqual = (a, b) => {
+    if (Array.isArray(a) && Array.isArray(b)) {
+      return a.length === b.length && a.every((val, index) => isEqual(val, b[index]));
+    } else if (typeof a === 'object' && typeof b === 'object' && a !== null && b !== null) {
+      const keysA = Object.keys(a);
+      const keysB = Object.keys(b);
+      return keysA.length === keysB.length && keysA.every((k) => isEqual(a[k], b[k]));
+    }
+    return a === b;
+  };
+
+  if (isEqual(parsedBody[key], value)) {
     return true;
   }
 
   if (interchangeableKeys.has(key)) {
     return interchangeableKeys
       .get(key)
-      .some((interchangeableKey) => parsedBody[interchangeableKey] === value);
+      .some((interchangeableKey) => isEqual(parsedBody[interchangeableKey], value));
   }
 
   return false;
diff --git a/api/server/middleware/enforceModelSpec.spec.js b/api/server/middleware/enforceModelSpec.spec.js
new file mode 100644
index 0000000000..04a8e5b35f
--- /dev/null
+++ b/api/server/middleware/enforceModelSpec.spec.js
@@ -0,0 +1,47 @@
+// enforceModelSpec.test.js
+
+const enforceModelSpec = require('./enforceModelSpec');
+
+describe('enforceModelSpec function', () => {
+  test('returns true when all model specs match parsed body directly', () => {
+    const modelSpec = { preset: { title: 'Dialog', status: 'Active' } };
+    const parsedBody = { title: 'Dialog', status: 'Active' };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(true);
+  });
+
+  test('returns true when model specs match via interchangeable keys', () => {
+    const modelSpec = { preset: { chatGptLabel: 'GPT-4' } };
+    const parsedBody = { modelLabel: 'GPT-4' };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(true);
+  });
+
+  test('returns false if any key value does not match', () => {
+    const modelSpec = { preset: { language: 'English', level: 'Advanced' } };
+    const parsedBody = { language: 'Spanish', level: 'Advanced' };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(false);
+  });
+
+  test('ignores the \'endpoint\' key in model spec', () => {
+    const modelSpec = { preset: { endpoint: 'ignored', feature: 'Special' } };
+    const parsedBody = { feature: 'Special' };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(true);
+  });
+
+  test('handles nested objects correctly', () => {
+    const modelSpec = { preset: { details: { time: 'noon', location: 'park' } } };
+    const parsedBody = { details: { time: 'noon', location: 'park' } };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(true);
+  });
+
+  test('handles arrays within objects', () => {
+    const modelSpec = { preset: { tags: ['urgent', 'important'] } };
+    const parsedBody = { tags: ['urgent', 'important'] };
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(true);
+  });
+
+  test('fails when arrays in objects do not match', () => {
+    const modelSpec = { preset: { tags: ['urgent', 'important'] } };
+    const parsedBody = { tags: ['important', 'urgent'] }; // Different order
+    expect(enforceModelSpec(modelSpec, parsedBody)).toBe(false);
+  });
+});